2-(3,8-Diazabicyclo[3.2.1]octan-8-yl)ethan-1-ol → HCID 86686634, compound

HRID 1850557Notes

Reaction equation

HRID 1850557 reaction equation
[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20](O)=[O:21])=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:25](=[O:29])[N:26]([CH3:28])[CH3:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:30]12[N:37]([CH2:38][CH2:39][OH:40])[CH:34]([CH2:35][CH2:36]1)[CH2:33][NH:32][CH2:31]2>>[CH:1]1([N:6]2[C:10]3[N:11]=[C:12]([NH:15][C:16]4[CH:24]=[CH:23][C:19]([C:20]([N:32]5[CH2:31][CH:30]6[N:37]([CH2:38][CH2:39][OH:40])[CH:34]([CH2:35][CH2:36]6)[CH2:33]5)=[O:21])=[CH:18][N:17]=4)[N:13]=[CH:14][C:9]=3[CH:8]=[C:7]2[C:25]([N:26]([CH3:28])[CH3:27])=[O:29])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 450994402-(3,8-Diazabicyclo[3.2.1]octan-8-yl)ethan-1-olHCID 583154726-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid

Product 1

HCID 86686634HCID 86686634, compoundYield 59%

Procedure

The 6-(7-cyclopentyl-6-(dimethylcarbamoyl)-7H-pyrrolo[2,3-d]pyrimidin-2-ylamino)nicotinic acid was combined with 2-(3,8-diazabicyclo[3.2.1]octan-8-yl)ethanol following amide formation method 3 which gave 7-cyclopentyl-2-(5-(8-(2-hydroxyethyl)-3,8-diazabicyclo[3.2.1]octane-3-carbonyl)pyridin-2-ylamino)-N,N-dimethyl-7H-pyrrolo[2,3-d]pyrimidine-6-carboxamide (18 mg, 59% yield). 1H NMR (400 MHz, CDCl3) δ ppm 9.00-8.87 (m, 1H) 8.87-8.78 (m, 1H) 8.57 (d, J=8.08 Hz, 1H) 8.44 (s, 1H) 7.79 (dd, J=8.59, 2.53 Hz, 1H) 6.54-6.43 (m, 1H) 4.81 (dq, J=9.09, 8.93 Hz, 1H) 4.51 (br. s., 1H) 3.82-3.49 (m, 4H) 3.40-2.99 (m, 10H) 2.69-2.44 (m, 4H) 2.16-1.99 (m, 4H) 1.91 (d, J=5.56 Hz, 2H) 1.83-1.45 (m, 4H); HR-MS (m/z MH+) 533.30 RT 2.56 min

Sources & evidence

ORD record
ord-76e826592ba54db48178f84d88d3a39c
Source dataset
uspto-grants-2015_02
Patent number
US08957074B2

Reaction notes

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